| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| TUE 9/10 | 4:00 PM | Varsity | League | Normal | Away | Cheshire | | | | Mercy High School - Cross Country Course | |
| Mercy | | |
| Wilbur Cross | | |
| TUE 9/17 | 3:45 PM | Varsity | League | Normal | Away | Hamden | | | | Hamden Middle School - Back Field | |
| Lyman Hall | | |
| North Haven | | |
| WED 9/25 | 3:30 PM | Varsity | League | Normal | Home | | | | | Guilford High School - Guilford Fair grounds | |
| TUE 10/8 | 4:00 PM | Varsity | League | Normal | Home | Lauralton Hall | | | | Guilford High School - East River Preserve | |
| Career Magnet | | |
| Shelton | | |